


The Best Whorehouse in Beacon

by DustinMcDreamy



Category: Teen Wolf (TV)
Genre: Alternate Universe - No Werewolves, Alternate Universe - Prostitution, Anal Fingering, Anal Sex, Angst, Blow Jobs, Dark, Dubious Consent, Emotional Hurt, Forced Prostitution, M/M, Masturbation, One Shot, Pain, Rimming, Sexual Abuse, Slow Build, Smut, Suicide Attempt, Threesome
Language: English
Status: In-Progress
Published: 2015-05-28
Updated: 2015-05-29
Packaged: 2018-04-01 12:23:10
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 10,807
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4019596
Author URL: https://archiveofourown.org/users/DustinMcDreamy/pseuds/DustinMcDreamy
Summary: <blockquote class="userstuff">
              <p>Stiles is a regular 21 year old college student who gets coerced into being a prostitute by a wealthy son of a CEO when his father ends up in the hospital. Now, Stiles has to adjust to pressures and expectations of being one of the Whittemore's whores, especially when Stiles finds himself caught in the dangerous crosshairs of Whittemore Sr. and the Hale family.</p>
            </blockquote>





	1. The Meeting, The Accident, and The Proposal

**Author's Note:**

> This FIC will have smut, fluff, good times, bad times, feels, drama, intenseness, and more. It is going to be an emotional rollercoaster. The plot will accelerate halfway through.

     Stiles opened up the fridge and took out the carton of concentrate that read "Very Berry Hibiscus". He poured the juice into the venti cup to where he was supposed to and then exchanged the berry juice for the lemonade. Usually this drink was made with water, but it tasted better this way, even though they weren't allowed to do it when a supervisor was around. Something about the lemonade being more expensive than water and there was no way to add lemonade on the register. Oh well. There will always be customers that want that 'secret menu' drink. He grabbed the tongs and plumped a few berries into the drink. The berries instantly began to dye the clear liquid. With a few shakes, the flavors all mixed and the drink changed to a cranberry color. Stiles handed the drink to the customer, the last customer in the shop, and wished her a good day. She thanked him, and left the store, leaving Stiles alone.

     Stiles began to get ready to close up the shop for the day. He was wiping down the counters and tables, placing the chairs upside-down onto them, which the openers would just have to take down again. He was sweeping the floor when the bell rang and a man entered.

     "You open?" the gentleman asked. He was the model type of man, around Stiles's age. His hair was gelled, looking suave and professional; he had sharp, fierce blue eyes that looked like they could kill a man with just a glance. His jawline was prominent and chiseled like marble and Stiles was having dirty thoughts about kissing on it or sitting on it. He was built, athletic, and handsome in his tailored suit, accented with a fancy watch. Stiles saw outside the windows at his car. Was that a Porsche? That was definitely a Porsche. Or was it? Stiles had never seen one before so he wasn't sure. 

     "Yeah, I can make you something, just let me wash my hands first," Stiles said as he set down the broom and went back behind the counter to clean off before re-entering the foyer. "What can I get for you, sir?"

     "I'd like a Grande Iced Skinny Mocha," said the man as he handed over his platinum credit card. Stiles couldn't help but try to glance a sneak peek at the name as he swiped it in the machine. 'JACKSON WHITTEMORE'. "I saw that," he smirked. Stiles became bright red. "It happens all the time when you got looks like mine."

     "I don't know what you're talking about," Stiles lied as he handed Jackson his receipts.

     "You're a horrible liar. Never do business. Sharks will eat you alive," Jackson retorted.

     "Rude. I am doing Corporate Communication and Public Relations," Stiles said as he was making Jackson's drink. "Sorry, there's just nobody else else here and I like talking and I can't stand awkward silence."

     Jackson chuckled. "I dislike it too, I just prefer to be the one to do the talking. There are two types of people: those who talk, and those who listen. I like commanding attention," Jackson said flirtily. Stiles blushed some more and handed Jackson his drink. Jackson cupped Stiles's hand as he took it and winked at Stiles before he took it out of Stiles's hands. Jackson sauntered out of the store with a certain swagger, and Stiles was checking out his ass on the way out.

     "My name is Stiles. Stiles Stilinski. Just so we're even," Stiles blurted out.

     Jackson was at the door, mid-push. The bell had rung and everything. He was on his way out, but he stopped mid-step. "Stilinski," he said slowly, emphasizing every last syllable of the name without eve looking back. "I know that name." And he continued leaving, door closing behind him, leaving Stiles alone in the coffee shop with a hardon for the handsome stranger.

**That was Stiles's first time meeting Jackson. That encounter would be Stiles's only fond memory of the man for a very long time.**

    The spring semester was ending soon, and Stiles was looking forward to the summer semester. He was not taking classes, and he would be able to work twice as much and earn extra money to save and stash aside for a rainy day. He was giving a customer a drink when his ringtone was going off. Stiles's heart sank in his chest. His phone was set on 'Do Not Disturb'. A phone call would only go through if his phone had been called more than once or one of the 'in case of emergency' numbers was calling. This particular ringtone was only set to two locations: the sheriff's station and the hospital.

     "I have to take this," Stiles said to his coworkers as he rushed into the back of the store. He pulled out his phone from his pocket and swiped the screen to answer. "H-hello?" he stuttered.

     "This is Beacon Hills Memorial Hospital. Is this Stilinski? We're not sure how to pronounce the first name," the operator asked.

     "Yes," Stiles replied bitterly and annoyed, "what's wrong?"

     "It's your father, John. He's been shot," the operator said.

     Stiles felt his chest tighten. The world around him grew silent, aside from a small ringing in his ears. His heart began to race and his hands were shaking. The phone fell out of his hands onto the ground and Stiles collapsed as well. His body began to force tears and screams out of his eyes and lungs. A coworker ran in to see Stiles having a panic attack on the ground. Stiles didn't remember what was going on around him. Only pain, only fear.

     A few hours later, after the panic attack had subdued and he left work and was able to get a hold of Scott, he was at the hospital where his dad was. His father was in a coma from the gunshot. Scott was holding Stiles, rubbing his back supportively as Stiles cried softly. A doctor came in, and stiles and Scott both stood up. She looked sympathetic for them as she approached and reached out her long hand.

     "Hello, Mr. Stilinski," she said. Her voice was strong, but still carried a pleasant tone. "I'm Dr. Malia Tate. I'll be your father's primary physician while he's here."

     Stiles nodded. "So, what's the damage we're looking at?" Stiles asked.

     "It isn't good, Mr. Stilinski," she said. "Whoever shot him hit a sensitive area for organs. There was significant bleeding out. From what I can tell, your father went into shock. Blood pressure got too low, and not enough oxygen. We got him in time before it could kill him, but as you can see, too much time had already passed. Comas are unpredictable. He could wake up soon, he could wake up in weeks, he could wake up never. If he does awaken, there is a possibility of some brain damage. I can tell you that from his scans, his brain does look pretty healthy, so not too much scare there if he does wake up. The only issue is waking him up."

     "Alright," Stiles choked out faintly, like a whisper because he couldn't muster up the strength to use his vocal chords properly. He was trying to fight his tears back so hard that the amount of pressure that was forming in his throat was so painful. He gasped for breath and Scott rushed over to hold him. Dr. Tate ran over to the water dispenser and got Stiles a cup of water to drink. "Thank you," he mustered.

     Scott accompanied Stiles home that night, making sure Stiles ate even though Stiles insisted that he wasn't hungry and making sure Stiles showered. In the morning, Scott had to nearly force Stiles out of bed, but he allowed Stiles to call in and take a personal day. Allison came over to cook real food that evening and give Stiles her support and prayers. Stiles had to manage on his own after that, and was back at work two days later.

     Benefit and support checks were coming in to pay for the Sheriff's medical bills, but they weren't covering what they needed to. A lot of California's money was currently being spent towards their water crisis. Beacon Hills was not excluded from those efforts. The city just wasn't putting up the money Stiles needed. There was also his upcoming tuition that had to be paid for. Stiles had set up a GoFundMe, and donations initially came in like crazy. Stiles was forever grateful, but over the initial hype, the donations stopped coming, and Stiles was back where he started. The mortgage bills were coming in, his father's credit cards, Stiles's credit cards. Stiles found himself stressed and overwhelmed.

     He was pouring himself a glass of his father's Jack Daniels when there was a ring at the doorbell. Stiles put the drink down and headed to the door. Looking through the stained and textured glass of the door, Stiles couldn't tell who was on the other side. He opened the door to find a familiar handsome gentleman and an asian girl in a beautiful cocktail dress and jewelry at his door.

     "Stiles Stilinski," the man said confidently.

     Stiles stared at the man for a few seconds with curiosity. "I've seen you before," Stiles said. "Porsche guy."

     "And now I'm porch guy," Jackson teased. "May my friend and I come in? I heard about your father and wanted to talk."

     Stiles hesitated, but he opened the door more and stood aside. He's not entirely sure why he did it. He didn't know this guy, not for real. And it was all very weird, but Stiles was curious. And Stiles knew that curiosity killed the cat, but he also knew that satisfaction brought it back. He wouldn't be able to send them away without knowing. He awkwardly led them into the kitchen where his bills and paper emss were embarrassingly scattered.

     "I'm very sorry about the mess. I, uh, wasn't...I wasn't expecting. Do you, would you like, uh.. want a drink?" Stiles nervously stuttered.

     "No thank you, Mr. Stilinski. I suggest you relax. You seem tense. May we have a seat, I have something important to discuss, and everything will make sense," Jackson said. Stiles nodded and gestured them to sit down. Stiles took a very large sip of his whiskey and grunted as he swallowed it. Jackson smirked at him. "I have a very uneasy confession to make, Mr. Stilinski. You may not want to hear everything I have to tell."

     "Just, do it, please," Stiles said.

     Jackson nodded and reached in his suit for a manilla envelope. He took out a small set of staple papers and handed them to Stiles. "These are your father's bank statements. As you can see, he has deposited many a large check amount from the account highlighted in yellow." Jackson handed him another set of papers. "These are the bank statements for that account. It is a decoy account owned by someone named Colton Haynes. Colton Haynes has many deposits from a Roy Harper. And Roy Harper has many deposits from...me." Jackson handed him even more paperwork and Stiles looked over everything.

     "How long have you been giving my dad money?" Stiles asked softly.

     "Years," Jackson said. "About 21. It started with my father," Jackson said.

     "Why?" Stiles whispered.

     "We invested in him. Your father was a mechanic before he was a cop. We hired him to go through Police Academy training and to be a spy and pay for his espionage and silence," Jackson said.

     Stiles looked at Jackson afraid, frozen in fear, tears coming out of his eyes. "Are you the fucking mafia?"

     Jackson chuckled. "No, we're not. We own....an escort business."

     "Escorts,....."

     "Is the delicate way of putting it," Jackson said stiffly. "We have one or two policemen under salary to keep an eye out for us. To protect us. Having the Sheriff was the best. Now he's gone, and the lack of security is hurting my business."

     "What does this have to do with me?" Stiles said.

     "I'm in the process of hiring more policemen, but that takes time. I need something to restart business right now," Jackson said. "I have........". Stiles saw Jackson lose all preparation and confidence in an instant. Jackson sighed and rubbed his temples, lost in thought. "Sorry, I was....unsure of how to say this, now. Unsure if this will work. Do you remember our conversation, Stiles? At Starbucks? I am not a shark. I can't just use people. I try to, but I am too soft. I'm never good enough. But there are sharks that want to bring down what I have. I have women like Kira here I look after, care for, and genuinely support. And that could all go to waste without you. You're an important cog in this machine. I will fail without you, and if one of those sharks sees me failing, they will bring all of it down for a laugh."

     "What do you want from me, Jackson?" Stiles asked.

     "I need something new to spark my business. Something to draw support and interest back in. Something to keep those sharks entertained. I need to bring in a male escort. I would like you to be that escort," Jackson said.

     Stiles just stared at Jackson, and then looked over at Kira. "Is this guy serious?"

     "I am willing to pay you the world, Stiles," Jackson. "All of these bills around you will be taken care of. I personally hand-select these gentlemen. They're all hot, nowhere near tragic, and will not hurt you. Stiles, you can go to school. Your dad will be healthy. Your house will stay yours. You'll even get extra money for yourself to stash. This only has to continue until your father wakes up.

     "What if I don't want to?" Stiles asked.

     "You struggle in debt," Jackson replies. "And you lose school, you lose your house."

     "What if I turn you in with this information?" Stiles asked.

     "Kira?" Jackson asked.

     "You lose school. You lose your home. When your father wakes up, he gets arrested . Jackson gets arrested. I get arrested. My family stops getting money from me. I have seven younger siblings back home and one parent. They starve. They suffer. There are three other innocent girls that get arrested. The innocent people they care about suffer. We are good people, Stiles. We just don't do good things."

     "I dislike being a shark, Stiles. But I like being a winner. I like the girls I look after. They are my pride, my joy, and it may sound weird and creepy, but my friends. I personally didn't arrange this, this was all my father. And this isn't the whole tree. There are more complicated roots. So much will go downhill. I take pride in what I do because if I don't I will not be able to live with myself. I was born into this, Stiles. And sadly, you were too. I knew when I met you, you were special. I recognized your name. I...I did not anticipate any of this. I wouldn't have asked for this. I wouldn't put you in your position intentionally. But we play with the cards we're given. I was given this prostitution ring as an inheritance. And you've been given an opportunity to help your father."

     Stiles poured himself another glass and drank it all. "All these bills, you'll lose money on me."

     "It isn't about the money, Stiles," Jackson said. "It's about the people. In high school I was a jock, a bully. I only cared about myself. I was broken myself, damaged, didn't need anyone. Then I turned 18. Inherited all this. Met people as broken as me as lonely as me. And I took it over because if we don't look out for and care for each other nobody else will."

     "He is my family, Stiles," Kira said. "Unconventional, but family. The work isn't pretty, but it's not torture. Sometimes it's nice, actually. We survive together."

     "So what do you say, Stiles?" Jackson asked.

     Stiles sat there, looking at Jackson and Kira, and then at all the bills. Stiles knew there was no way in hell he would want this for Stiles. Stiles didn't want his father being a dirty cop who took bribes, but he did it to support Stiles. Stiles has sex for free. He's fucked strangers for nothing. He's had his shames and his delights before.

     "Okay," Stiles said. "I'll do it."

* * *

 

     Dr. Tate entered the Sheriff's hospital room with a clipboard. A tall slender, brunette in leather was standing over him. She smirked at Malia as she shut the door and got closer.

     "Are you Dr. Tate?" the woman asked.

     "Who's asking? Visiting hours are over," she replied.

     "My name is Katherine," she said.

     Malia extended her hand. "Katherine, I've heard great things. Nice to officially meet you in person. I assume we'll be seeing each other often."

     "Indeed we will," Katherine said. "My employer wants a full report."

     "As far as damage goes, you got him a good spot. No severe injuries. He'll be very healthy when we choose to awaken him," Malia said.

     "So your medically induced coma is working well for us?" Katherine asked.

     "Absolutely," Malia said. "Appearance wise, he's a lost cause. Nobody will raise too many questions. He won't wake before we officially decide to awaken him."

     "I'll let the employer know. Bonuses will be awarded to your account, as usual. We'll be in touch," Katherine said as she left.

     "Good night, Sheriff Stilinski," Malia said as she followed.


	2. The Arrival, The Girls, and The Preparations

**Summary for the Chapter:**

> Stiles arrives at the Whittemore Mansion and meets the women who work for Mr. Whittemore as well as tries to deal with his nerves for the upcoming giant Whittemore party.

     Stiles was upstairs in his bedroom folding, rolling, and packing his clothes into his suitcases. Stiles would be living at the mansion Jackson Whittemore had set aside for his 'employees'. He said it made clients feel more at ease in a home environment, and it was better for the girls. He zipped up his 3DS in its case and wrapped the charger around it before he placed it in his duffle bag as Kira knocked in the entryway.

     "Hello," she said softly. "Is it alright if I enter? Maybe help?" Stiles nodded and she entered cautiously, as if literally walking on eggshells. "Do you need any help?" Stiles just shook his head and zipped his duffle closed. He had a few more things to go through. Kira sighed and anxiously looked around, biting her lip. "I'm sorry," she apologized. "This, what you're doing, it isn't easy. And it's sudden. And it's...kind of forced."

     "Kind of?" Stiles interrupted, looking away from his baggage to give her a stink glare. Kira frowned and avoided his gaze. 

     "Mr. Whittemore is not a bad person, Mr. Stilinski," Kira said. "And you'll learn a lot about him. You'll learn things I'm not in the right place to disclose. I tell you, if he could stop this arrangement he would. The whole lot of it. You, specifically, this wasn't an overnight decision for him. His father suggested it, when they were creating a plan together. Mr. Whittemore had negotiated dozens of alternatives, but Sr. Whittemore wouldn't have any of it."

     "I take it Sr. Whittemore started this business? Was the one to uh,....hire my father as an officer?" Stiles asked. Kira nodded. Stiles let out a huff of angry air and zipped his large suitcase shut.

     "I would have hated to been here when Sr. Whittemore was in charge. He's.....cruel," Kira said delicately.

     "A shark?" Stiles asked. Kira looked pensive, not fully understanding Stiles and Jackson's inside references but nodded. Stiles stood up from his floor and yanked the suitcase and the duffle off of the bed. He started headed to the door when Kira blocked him and she put his hand to his chest.

     "Just remember, Stiles. You have friends. I assure you, I am here for you. The other girls, they'll likely come off cold first. They think the idea of a guy coming to work with us is funny. You might be their chew toy. But I am here for you, Stiles. The first uh, client is going to be the most difficult. And I'll be here. And then soon, you won't need me to be. But I'll still be there," Kira said comfortingly.

     "Thank you, Kira," Stiles said. Kira nodded and they headed downstairs where Jackson was. He was sitting on the Sheriff's recliner, doing something on his gold iPhone. Honestly, it kind of hurt Stiles a bit to see someone in his father's spot. But Jackson wouldn't have known, and Stiles didn't want to bring it up. Jackson stood and smiled.

     "Are we ready to go?" Jackson asked. Stiles nodded. Jackson started walking towards them and grabbed Stiles's duffle bag. "Kira, roll the suitcase."

     "It's ok, I got it," Stiles said. Jackson nodded and headed towards the door. Stiles turned off the lights and locked the door. There was a red, four door corvette in the driveway. "Where's the Porsche?"

     "I wanted to lay low. Be discrete," Jackson said.

     "Right," Stiles said dryly. "You tried."

     They put the luggage into the trunk before getting into the car. Kira took the back seat, allowing Stiles to take the shotgun spot. Jackson started the car and took off. After fifteen minutes of driving, Stiles turned to Jackson. "Where are we going?"

     "Beacon Heights," Jackson replied.

     "Rich people county. Groundbreaking," Stiles replied. Kira laughed from the back.

     "You asked," Jackson said. 

     Stiles had only been to Beacon Heights once, as a kid, and it was because the airport was a little past their aristocratic city. Stiles was in awe as Jackson drove onto the giant, beautiful bridge. Every bracing, beam, and post was illuminated with different colored spotlights that made the bridge look like a rainbow. As they drove off the bridge, they were immediately in a glamorous town, welcomed with a large three-tier water fountain that had glistening, crystal clear water spraying out like an umbrella style waterfall.

     "This is fucking beautiful," Stiles said. 

     "Is it too showy? Us rich people can be cocky and flamboyant," Jackson said.

     "I'm okay with it for now," Stiles replied.

     A few minutes later, and Jackson was pulling up into the driveway of a big mansion with a four-car garage. The three of them were getting out of the car. Jackson grabbed the suitcase and the duffle and set them by the door. "I'll have Jarvis get these in a bit. I'd like to give you a tour, Stiles." Stiles followed Jackson down the hallway until they entered a large room full of sculptures artwork, and glass cases. "This is the art exhibit. Clients love it. It elevates mood comfort, their egos, and the amount they pay me," Jackson said.

     "I admire the honesty," Stiles said, examining everything. "This is all so beautiful."

     Jackson's smile lit up. "I'm glad you like it. Those two doors lead to Lydia's room and Kira's room. Up this staircase is our theatre. It's nothing too special, and Kali and Erica's rooms. Let's head to the west wing, Stiles." They began to walk and they entered the main foyer. There were a few lounges, a day bed, glass cases with glassware and china, and a few potted plants as well as a grand staircase. "This is just our entryway foyer. Up the stairs is my bedroom, my office, and the balcony that faces the backyard which has so much to offer. That's where the majority of the entertaining takes place."

     "Outside!? In public?" Stiles said alarmed.

     "Yeah, we get such nice weather and....OH!" Jackson exclaimed, catching on. "Not, not the actual. Uh, yeah, no. We hold parties. To mingle with clientele, potential clientele and to sort of hide everything. If we can make it appear people are just hooking up at parties, it's better for us. But they're very exclusive. Part of your duties will be to host and entertain as opposed to and addition to...hosting and entertaining. Do you copy?"

     "Yeah, I think so," Stiles said.

     "Great," Jackson said, continuing the tour. "This is our kitchen and dining room. Jarvis cooks and serves us but we really don't eat together so we don't use the dining room much."

     "Shame, it's elegant," Stiles said as he and Jackson continued forward. 

     "This room is our home gym. We have a few machines. You are getting this spare bedroom next to it," Jackson said as he opened the door. The room was painted a sapphire blue and had white carpeting. A large, king sized bed with a canopy and curtains was nearly the only thing in the room aside from a dresser, a closet, a night stand, and the door to a bathroom.

     "Damn, that's a large bed," Stiles said as he got closer. It had sapphire and navy stripes on it to coordinate with the walls. Stiles pushed on the mattress a few times. It felt extremely comfortable. Stiles was a little nervous that he'd be fucking strangers on this bed and sleep in it. But he had done that with his bed back home, why was it so different? 

     "Are you ready to see the backyard?" Jackson asked.

     "How impressive can it be?" Stiles asked.

     "Like Gatsby," Jackson said enthusiastically. They headed through the kitchen and onto the outdoor patio. It took a while for Stiles to gather it all in. the first thing Stiles noticed was the giant pool in the middle with diving boards. It was an impressive size. Stiles turned the corner to check the center of the patio. There was a very large DJ booth and a dance floor installed onto the patio. Continued along that direction were massage beds and chaise lounges lined up along the side of the pool.

     "Massage tables?" Stiles asked.

     "It helps the guests unwind, plus, everyone loves massage fantasies," Jackson said. Stiles continued walking along the pool parameter. On the corner of the property was a romantic garden area with hedge sculptures, a tent, a picnic table, and campfire. Stiles walked away from it and got near a hot tub and an outdoor sauna.

     "We got summer camp, a spa, a club. This is ridiculous," Stiles muttered under his breath. He kept walking and laid his eyes on the next section and muttered under his breath. "Son of a bitch." There was a Japanese hot spring tucked in the middle of several trees, all making a canopy above it with a sand Zen garden not far from it. "Who the fuck builds a hot spring and a Japanese Zen garden? Fuck rich people."

     Stiles headed back to the patio where Jackson was pouring drinks from the minibar. "How do you like it?" Jackson asked.

     "It's excessive and over the top," Stiles replied.

     "I take it you mean that in a bad way," Jackson said. "Money is like a penis, Stiles. If you have a lot stashed, you show it and you let people know. Speaking of which, you obviously have a nice, plump bubble ass. What are you packing in the front?" Stiles rolled his eyes and looked away from Jackson as he undid his pants and let them and his boxers drop. "Nice, we can work with that." Stiles redressed himself as a redhead and a blonde walked out, dressed to the nines in couture.

     "Don't stop on our accounts," the blonde said. "We want to see too!"

     "Speak for yourself, Erica," the redhead retorted.

     "Stiles, this is Lydia, our star, and Erica. Be cautious, she bites," Jackson said. Erica grinned by mouthing a fake chomp towards Stiles.

     "Hi," Stiles said awkwardly.

     "I went from 'Wow, what a cutie' to 'Oh no, he's hot' to 'Protect him he's awkward'. You need to get some confidence in this business. Jacky, do you even know if he's good in bed?" Erica teased.

     "Regardless of his talents, he's very aesthetically pleasing in all directions. And I could use somebody submissive who listens," Jackson argued.

     "Whatever you say," Erica said, eyeing Stiles up and down with judgement.

     "I'll be in my room," Lydia said dryly. "Do not disturb me." She turned around and sashayed away from the rest of them. 

     "So, Stiles," Erica said, twirling her hair playfully. "What would you like to do tonight?"

     "I'd actually just like to get to bed," Stiles said. Erica chuckled. 

     "Rest for your big day, tomorrow, Batman," she said teasingly as she sauntered inside the house.

     "I take it that means I start tomorrow?" Stiles asked. Jackson slowly nodded.

     "We're having a party tomorrow night. You'll get your first client. I hand picked him. He's a great friend of mine. Great in bed, so don't worry there. He's a high school friend. Made me realize I was bisexual. His name is Daniel Mahealani. He's Hawaiian. He's gentle. A little too much for my liking, but a great start," Jackson said.

     "Alright, I can do that," Stiles said.

     "I'm waking you up at 8 in the morning. Jarvis will have breakfast ready. I need the maid to measure you so we can get you something nice to wear for the party. Also, how do you feel about jockstraps?" Jackson asked. Stiles was blushing.

     "Well I don't own one, but they're...they're hot I guess," Stiles said.

     "I'm going to pick you up a few pairs from the underwear store. Small or Medium?" Jackson asked.

     "Whatever a 28 is," Stiles responded.

     "Alright. Have a nice night, Stiles," Jackson said. Stiles headed to his new room and locked the door behind him, just in case the girls were going to play a prank on him. He wouldn't put it past Erica, and he had only known her three minutes. His bags were set on his bed and Stiles worked on putting everything away and neatly stored before getting undressed and climbing into his new bed. He was nervous about this arrangement. His heart was racing. He got out and went into his medicine cabinet in the bathroom and took out two sleeping pills. His anxiety often kept him up, especially recently. He dry swallowed his medication and climbed back into the bed and rested his eyes, trying to calm down.

     Stiles woke up to knocking on his door. "Stiles, it's Jackson, wake up. We need to get you ready."

     Stiles groaned and slowly sat up. "I'm coming!" Stiles jumped out of bed and put on a T-shirt and some shorts before opening the door for Jackson. 

     "Evangeline, this is Stiles Stilinski. He's our newest resident. Let's get his measurements," Jackson instructed. Jackson gestured for Stiles to take a few steps back, and had Stiles lift up his arms so Evangeline could get the tape measure and get Stiles's dimensions. She wrote them down and handed them to Jackson.

     "Perfect. Stiles, I am headed to the store to pick up some clothes for you to wear tonight and well, all the time when I need you to. Stay out of trouble," Jackson instructed.

     "Will do," Stiles said as Jackson and Evangeline left his room. Stiles was tempted to back asleep, but he smelled waffles and headed to the dining room. Kira was there with her laptop and plate of breakfast and she smiled and waved when she saw Stiles.

     "Good morning, Stiles!" Kira exclaimed. "Did you sleep well?"

     "Once I took some sleeping pills, sure," Stiles said. "May I sit here?"

     "Of course!" Kira said cheerfully. Stiles slid in the seat next to her. 

     "What's that?" Stiles asked, gesturing to the computer. Kira blushed and shied away from Stiles.

     "Oh," Kira chuckled. "I uh-I write. Or I try, I'm not...I'm no Fitzgerald or Salinger. But I try. I'm trying to get published."

     "What is it about?" Stiles asked.

     "It's about a girl. She's like a god. She plays the role of judgement. And she has the ability to save people's lives, but in order to do so, she has to choose someone to die. And she knows like everyone's histories and the weight of deciding who does deserve to die is on her, and she has this guilt. And then suddenly, halfway through the novel, she notices her sister is marked for death along with all these people that are supposed to be on a train. It's going to be a big accident, a huge calamity. So she has this mission in bulk. She wants to save as many people on this train as possible, but she needs alternatives for every single one, so now she has to decide who is most worthy of being salvaged by going into their timelines and looking at their history and life. And she also has to decide if saving her sister is too biased. I'm trying to make it very emotionally wrecking. The feels, you know?" Kira asked. "Is it weird?"

     "Absolutely not! That's sounds so badass. You better get published!" Stiles said. Kira beamed with happiness. "Thank you! Honestly, I've never told the other girls I write. Is that, weird? I love them to death, but I feel like they wouldn't care or they'd think I'm weird. I'm the newest, too. Aside from you."

     "Well, I'm glad you trusted me with that," Stiles replied.

     After breakfast, Stiles got dressed in his fitness clothes and went into the home gym. There was a very tan woman with long, silky black hair running on the treadmill. She looked up at Stiles and hit the stop button as well as removed her headphones. "You must be Jailbait," she said viciously. Stiles looked at her curiously. Lydia, Erica, Kira, they were all in their low to mid twenties. Kali was at least thirty. She was beautiful for thirty, but you could tell she was getting seasoned.

     "You must be one of the Golden Girls," Stiles retorted. Kali's smug smile started to fall flat. 

     "Yes," she said sternly. "I've been here since before Lydia. I've been here before Jackson inherited the mansion three years ago. I was here with girls like Braeden, Jennifer, Marin. When they stopped making money, they were replaced. When I stop, I'll have to leave too. But I'm still making money, honey." She playfully slapped her hand on his cheek in a condescending manner as she headed to the door.

     "It's okay to be afraid to stop. I'm afraid to start," Stiles said. Kali paused for a second, just a split moment, before continuing and slamming the door. Stiles felt bad immediately afterwards. He crossed a line, but she attacked him first. He knew he wasn't liked without a chance, so he was going to reciprocate. Stiles tried to exercise his stresses away, but he couldn't shake away the entirety of his nervousness.

     Stiles headed to his shower afterwards, and Stiles swore he could get used to that. It had the perfect water pressure and water amount being sprayed on his body. It spread perfectly and wasn't just a stream on one part of his body. It was doing good at relaxing him, but not quite enough. Stiles cupped his dick and started to stroke himself slowly, occasionally tugging on his balls and then switching to play with one of his own nipples. He took deep breaths and picked up the pace. He didn't want to be ejaculating too early tonight if he had to please. Within a few moments, Stiles had his dick throbbing with pleasure, and with an electrifying sensation, he was coming over the shower floor, the water washing Stiles's come down the drain. The chill that ran its course through Stiles's body had loosened his nerves and untensed his him. He took a  final deep breath and turned the water off before drying himself and exiting.'

     To his surprise, Jackson was standing in his room with a multitude of colored shirts and ties spread along his bedside. Nervously, Stiles went to cover his junk by instinct, but then realized not only was he in a towel, Jackson had already seen his dick. Stiles had willingly showed him. Stiles saw Jackson faint lick his lips. That was likely subconscious. Jackson may not have known he did it. But Stiles knew Jackson was checking him out in the torso area, and Jackson was definitely aware of that.

     "I'm liking the top half," Jackson said as he got closer and brushed his fingertips along Stiles's chest and running over the bump of one if Stiles's nipples, tracing circles around it a bit. "You're so gorgeous, Stiles." Stiles felt himself rehardening underneath the towel at Jackson's attention. Jackson headed back to the clothes on the bed before Stiles was full-on rock. "I want you to wear this red. I want you to stand out tonight, command attention."

     "Sounds like somebody I know," Stiles said with a lump in his throat. Jackson smirked. 

     "I also got you some jockstraps. I'd say I want to see how they look on you, but....I don't want to cross lines," Jackson said in a soft tone.

     "The pimp doesn't want to cross any sexual lines?" Stiles teased.

     Jackson chuckled. "Get dressed, and hang the rest up. We have company in an hour." Stiles took a deep breath and shook his head. "You're going to do fine."

     "Alright, sir," Stiles said. Jackson winked as he left the room. Stiles nervously looked at the clothes and took another deep breath. "I am going to be fine. I am going to be fine. I can do this." Stiles dropped his towel and started to slip into his attire. When he got the red button-down shirt, tie, vest, dress slacks, and shoes on, Stiles looked at himself in the mirror, possibly the last time Stiles would be able to do so with dignity.

* * *

 

     Katherine let go of the hair curler and pulled it. Her golden highlighted air fell from the iron and swung gracefully to her neck. She turned the iron off and grabbed a small tube of red lipstick, and ran it across her lips, coloring them. As she pressed her lips together, Allison entered the room with a knock.

     "Scott and I are headed back home for the night. I'm really glad you're back in town," she said.

     "Well I am glad to be back for business, that's for sure. And that Scott is such a dollface. Hold onto him or I may just have to take him from you," Katherine teased. Allison laughed.

     "I don't think you need him. You're clearly headed for a date. Who's the lucky guy?" Allison asked. "You look so beautiful. He's going to love it."

     "Well thank you, darling. I did put a lot of time and effort into this look. But I don't exactly have a date tonight," Katherine said.

     "No?" Allison questioned. "What's the occasion?"

     Katherine dipped a brush into her container of blush and set the powder to cheeks as she smiled in the mirror. "I'm headed to a party."

**Notes for the Chapter:**

> Some of you were asking about the endgame here. I do not want to spoil for everyone, so if you message me on Tumblr or Twitter at "sterekorgtfo" I can let you know without spoiling for everyone. I don't want to spoil anything because I have MANY twists and turns headed your way! There will be no update until late 5/30 due to work. Chapter Three will have images of the Sims version of this mansion as well to get a good sense. This chapter didn't have much action, but Chapter Three will.....in many senses of the word.....


	3. The Guests, The Nerves, and The Sex

**Summary for the Chapter:**

> The party kicks off and Stiles wanders around, meeting other clients and intermingling with the girls, anxiously waiting for his cue from jackson to meet Daniel and have sex for the first time as a prostitute.

**Notes for the Chapter:**

> There is a chapter that goes along with the smut at the end, don't just be skipping it just to get to the hot Danny/Stiles action I know you horndogs are looking forward to ;)

**An hour before the party**

     "Stiles, we need to go over some precautions," Jackson said. "Condoms and lube are in your nightstand. Do not under any circumstances ever let anyone fuck you without them. Second, don't worry about how the money goes. Everything is prepaid and goes through me and I put the money in your account. You're getting three grand. It's usually more, but the bills back at your dads and what not." Stiles was trying to burst from freaking out. Three thousand dollars for one hookup? This would possibly not be that bad after all. "Stiles, presta attencion!" Jackson said as he snapped his fingers in Stiles's face. "Next, do NOT under ANY circumstance refer to the girls by their real names. Lydia is going to be Holland. Repeat that."

     "Holland," Stiles said.

     "Kira is going to be Arden," Jackson said.

     "Arden," Stiles repeated.

     "Kali is going to be Felisha," Jackson said.

     "Felisha," Stiles said.

     "Your name is going to be Dylan," Jackson said.

     "Dylan," Stiles said.

     "What are they?" Jackson asked.

     "Lydia, Holland; Kira, Arden; Kali, Felisha; I am Dylan," Stiles said.

     "Good," Jackson said. "Now, not everyone here is a client. These are also mixers for mine and my father's company. Be discrete. Don't run your mouth. We operate under a veil. Don't ruin the veil."

     "Got it," Stiles said.

     "Keep your phone on you. I'll text you when and where to meet Daniel. Until then, you're welcome to socialize. Don't get drunk but a drink or two will be fine."

     "You got it, sir."

**Now**

Stiles was roaming among the crowd of men and women in high end tuxedos and cocktail dresses in search of a distraction of some sort. It was ironic in a sense-such a large party with a hundred or more people and Stiles had nobody to talk to. He passed by the Japanese tea table when Kira whistled at him and gestured him to come over.

     "Dylan!" Kira exclaimed. "I want you to meet somebody. This man here is Mr. Daehler. He's a frequent guest of ours. He's very good friends with Mr. Whittemore. Mr. Daehler, this is Dylan, our newest associate."

     Stiles caught on fast enough. Obviously, it was important to be on good terms with people who frequently fund his new boss's cause. Stiles extended his hand. "It's a pleasure to meet you, Mr. Daehler. We are delighted to have you in our company this evening."

     "Please," he said. "There's no need to be so formal with me." He leaned into Stiles's ear. "Considering what we all do here." Stiles nodded as he pulled back. "You can call me Matthew."

     Stiles nodded and smiled. "Well then, Matthew, what brings you indoors? The weather is warm, we have the music outside."

     "I tend to stay away from pools. Irrational fear. It's just currently too crowded for me to risk. And besides, this artwork is beautiful; and I'm not just talking about Arden. Whittemore alternates his exhibits every so often so this is all new. And I do like Arden and I pouring each other some delicious tea. You must have some." Matthew poured Stiles a small size of tea in the round bowl cup. Stiles bowed to Matthew and said his thanks before drinking it. It was warm and rich in smooth herbal flavors. It was slightly bitter for Dylan, but he didn't have any other complaints.

     "This is very good," Stiles said. 

     "So, Dylan," Matthew said. "Are you entertaining any guests tonight?" Matthew said. Kira blushed and his behind her paper fan.

     "A gentlemen would not kiss and tell or boast of his interpersonal relations," Stiles said. 

     "I respect that, sir," Matthew said with a bow.

     "I will leave you two now. It was wonderful meeting you, Matthew. You are always welcomed here," Stiles said as he got up and continued walking. He headed outdoors and walked near the masseuse tables. Lydia was there in a bikini and a man was laying on his back. Lydia was oiling up her hands when she spotted Stiles.

     "Aiden, this is our newest friend, Dylan. Ethan finally has somebody to play with so he can contribute back to all the alcohol he drinks here," Lydia said.

     "Hello, Dylan," Aiden said. "You are a bit of a stud. Ethan would love you. Aren't you going to screw his boyfriend tonight?"

     Stiles had a panic. Was he? Was he going to be a homewrecker? Was Daniel using Stiles to have an affair? "I don't know the personal affairs of  anyone in attendance of this party, nor do I know this Ethan or to whom you are referring." Aiden chuckled at Stiles and Lydia began to rub down Aiden's pecs.

     "Relax, Dylan," she said in an annoyed tone. "Daniel and Ethan have an open relationship. You're not a dirty whore yet."

     "Holland," Stiles said. "We need to be mindful of what we say."

     "I don't give a fuck, Dylan," Lydia said. "You are going to walk away. I'm going to use the stress of talking to you to get real deep in Aiden's skin to loosen him up, and then he's going to loosen me up and fuck the stress right out of me from behind." She winked at Stiles before gesturing for him to walk. Stiles rolled his eyes and started to continue his route.

     "I'll put in a good word for my brother, bro!" Stiles heard Aiden exclaim as he walked away. Already another potential client on Stiles's list made Stiles remember that this is not a one and done thing. This was going to happen a lot. This was the first of many parties. And this was going to take as long as it would until his father woke up from his coma. Stiles was getting overwhelmed all of a sudden, and needed a drink. He headed straight to the bar where he saw Erica laying across the bar in nothing but a bikini.

     "Dylan!" she yelled. "Do a body shot off of me!" The group of guys and girls around her started clapping and cheering Stiles on.

     "I think I'm going to have to pass," Stiles said. He was responded by a large chorus of 'boos'.

     "Dylan, you're my new friend, just please do it for the crowd! Do it! Do it!" Erica chanted. The group started to join her in their chanting and Stiles had no choice but to give in. Erica held the lime in her mouth and salt was sprinkled from the top of her bikini line to her belly button. A muscular black man poured the tequila into her navel and Stiles began to lick the salt trail up to it, slurp his apparent new friend's stomach, and nearly kissed her taking the lime out. The audience roared and cheered and Stiles nervously stepped back.

     "Are you going to be next, babe?" Erica asked the black man, stroking his face. He shook his head no.

     "I'll let you share your beauty to everyone now, because later I'm going to have you all to myself" he said.

     "Boyd's such a giver," Erica said with a wink and a giggle. "Who wants to go next?"

     Stiles quickly got away from that crazy Spring Break of a show. Stiles was headed straight back to his room but he remembered he'd have to be fucking someone there later and that wasn't sounding ideal at the moment. Where in this house could he be alone? He entered the gym room they had and then collapsed on one of the mats. He took deep calming breaths to himself. Stiles had never been a partier. Social environments like this made him really nervous and uncomfortable. His heart was racing, he was so nervous.

     The door swung open and two people were laughing as they entered. It was Kali and a man. She looked over at Stiles and jumped out of fright. "Jesus fucking Christ St...." She shook her head in annoyance, stopping her slip up. "What are you doing here?"

     "I needed a break from the party," Stiles said.

     "You have your own room," Kali argued.

     "As do you," Stiles retorted. 

     Kali puffed and exhaled before turning to her man. "Ennis, can you give us a minute and get me a drink?"

     "Yes. Fix the problem, Felisha," Ennis said as he left. The door closed and Kali looked angrily at Stiles.

     "Did Jackson not tell you the gym was off limits? Ennis reserves this. Fitness is his roleplay," Kali said.

     "No he didn't" Stiles said as he got up. "Fine I'm out anyways." Stiles tried to get past her but she blocked him and grabbed his shoulders, shook her head, and took a deep breath before looking at Stiles in the eyes. "The first time is the worst," she said in a supportive tone. "What we do isn't easy. It isn't pretty. Nobody chooses this life for fun. But you're doing this for your father. We all have our anchors we channel to get ourselves through this. Our anchors keep us strong. They keep us sturdy when we want to falter. They keep us from drifting away into a sea of shame and self-hatred. Hold onto that. What you're doing isn't awful. You're helping your father. And besides, sex is fun. Keep telling yourself that, trust it helps. We've all slept with awkward people in our past for free, might I add. Own your pride, own your sexuality. You are an art exhibit someone is paying to enjoy because you are a luxury, a vacation as opposed to an object. There's silver linings, Stiles. Hold onto them."

     "Thank you, Kali," Stiles said. "I appreciate it. I'm sorry we got off on the wrong foot."

     "I was in your spot too, once, and I had a rude bitch help me, so I guess I gotta keep the tradition going," she said with a chuckle. "Now for real, scram!"

     Stiles nodded and exited just as Ennis was returning with a drink. Stiles went the direction where they wouldn't cross paths. Suddenly, his phone started to ring.

FROM: JACKSON "COME UPSTAIRS TO MY ROOM. DANIEL IS HERE."

     Stiles continued his calming breathing before looking up at the large staircase that led to Jackson's area of the house. He slowly went up the flight of stairs which brought him to a small area which divided of two rooms. One door was closed and the other was open and he heard talking, Jackson's voice specifically. Stiles walked over and gently knocked on the door. He saw Jackson and a gentleman who Stiles assumed to be Daniel. The man was tall, built, tan, and handsome. Stiles instinctively smiled at his attractiveness, and felt himself blush. Daniel picked up on this and started smiling as well. Perhaps this was going to be easier than Stiles imagined. Jackson seemed happy by this.

     "Dylan, come in," Jackson encouraged, gesturing Stiles to enter. Stiles nervously approached, keeping his head down a  little before he was close enough for that to be considered too awkward. "Dylan, this is my good friend Daniel."

     "It's a pleasure to meet you," Stiles said, reaching out his hand to shake Daniel's. Daniel responded with the typical firm handshake.

     "Daniel, you are Dylan's first client so I expect a full report. Don't dissapoint me, Dylan," Jackson said.

     "He's going to be in very good hands," Stiles said confidently with a wink as he took Daniel's hand and escorted him out of Jackson's room.

     "Is there anything you'd like me to know before we both get started?" Stiles asked as he and Daniel entered Stiles room. Stiles closed the door and locked it and then looked back at Daniel.

     "I want you to know that I can tell you're nervous," Daniel said.

     A smile crept on Stiles's face. "No I'm not," Stiles lied.

     "You're a bad liar," Daniel retorted. "And it's okay to be nervous. All the bad things on the news." Daniel stepped a little closer and gently lifted Stiles's head up by cupping his chin, his other hand gently sliding down Stiles's arm reassuringly. "I'm going to take good care of you."

     Daniel leaned in to press his lips against Stiles's. It was soft at first, and Stiles took a small second to kiss back tenderly. Daniel responded with kissing Stiles more passionately, as opposed to like Stiles was made of fragile glass. Stiles wrapped Daniel around his arms and toured his hands all along Daniel's back during the kiss. Daniel slid his hands around Stiles's waist and cupped Stiles's ass, giving it a gentle squeeze that made Stiles jump a little, but also put more fervor into Daniel's mouth. Daniel pushed his hardening groin into Stiles's, indicating he was ready for more. Stiles unbuttoned Daniel's suit jacket before breaking the kiss.

     "What should we do with that? Everything on you looks expensive, I don't want it getting ruined or-" Stiles was cut off by Daniel's laughing. He just shook his head at Stiles and threw it on the ground.

     "The only thing getting ruined tonight is your ass" Daniel said with a wink and the return of the kissing. Stiles moaned deep in his throat and responded by very eagerly unbuttoning all of Daniel's shirt, then shucking it off his shoulders to reveal his muscular torso, complete with the hottest pecs and abs Stiles had ever seen.

     "Fuck yes" Stiles said as he removed his mouth from Daniel's lips, placing them on one of Daniel's nipples, kissing and lapping it up with his tongue as Daniel raked his fingers through Stiles's hair. Stiles roamed his hands and fingertips up, down, everywhere on Daniel's stomach and chest as Stiles began kissing his way down onto his knees. Stiles quickly unfastened Daniel's belt and undid his pants, yanking them to the ground to reveal Daniel's erection through his boxers. Stiles licked the bulge and pressed his mouth to the cloth, moving along the length of the shaft. Daniel yanked Stiles back up to unbutton Stiles, making him equally as shirtless.

     "You have a wonderful body, Dylan," Danny said as he played with Stiles's nipples and attacking his neck with his mouth. Stiles let out a moan before Daniel hooked his hands under Stiles's ass and lifted him, carrying him to the bed and thrusting him down on his back.

     "What happened to gentle?" Stiles teased. Daniel looked panicked.

     "Was that too rough?" Daniel asked, worriedly.

     "No, that was hot as fuck," Stiles said.

     Daniel grinned eagerly. "I can get rougher." He climbed over Stiles's body, making his way up to Stiles's face. He straddled Stiles's shoulders, reached for the back of Stiles's head, and brought it up to his clothed erection, bobbing Stiles's face into his cock. "You like that? Come on, use your mouth."

     Stiles was opening his mouth licking frantically, trying to get any part of Daniel in his mouth. "I need it, Daniel. I want the real thing. Please give it to me, Daniel."

     "Stick our tongue out," Daniel replied. As Stiles obeyed Daniel slowly slid his boxers out until his hard dick could spring free, slightly bouncing in the air. Daniel grabbed his cock, and hit it a few times on Stiles's tongue before he turned Stiles's face and hit his cheek. This made Stiles smile a bit. Daniel put Stiles head back and leaned over Stiles to angle his body so her could perfectly fuck Stiles's face. As he moved his hips back and forth, Daniel slid in and out of Stiles's eager mouth as Stiles sucked bobbing his own head, trying to use his tongue to massage Daniel's cock at the same time. Daniel began to pick the pace up a bit while additionally squatting closer to Stiles so his dick could go deeper into Stiles's throat. Stiles's throat began to make small noises as Stiles slightly gagged on it. "That's so fucking hot. Take my dick straight down your throat. God, I can't wait to have this inside your hole."

     Stiles's cock was twitching with excitement in his pants. After a whole day of worrying, he was actually excited to be fucked. He grabbed Daniel's ass with both hands as Daniel continued to fuck his mouth. After a few more seconds, Daniel climbed out of Stiles an embarrassing bridge of saliva and precum still connected Stiles's lips to the head of Daniel's cock. "Fuck my ass, please Daniel," Stiles begged. "I want you inside of me for real."

     "You're so impatient, Dylan. Are you trying to rush me and get me out? I haven't even gotten to enjoy your cock yet," Daniel said as he undid Stiles's pants and yanked them off of Stiles. He laid down on the bed to the side of Stiles, leaning himself over his dick. He grabbed Stiles's cock in his hand and licked a stripe up from the balls to the head before twirling his tongue around a few times before taking Stiles in his mouth. Stiles moaned and bit his lip as Daniel bobbed his head, taking Siles deeper into his mouth and then retracting his head to do it all again. Stiles moved his hips up to stay full into Daniel's mouth. Daniel slid one of his hands under Stiles, now that his pelvis in the air game him space, and felt around Stiles's ass. He took a finger and slid it up and down the cleavage of Stiles's bubble butt before playing with the muscled ring at Stiles's hole. Stiles moaned some more, bringing his hand to grasp at Daniel's head.

     Daniel removed himself and climbed over Stiles, kissing him everywhere on his chest before getting to his mouth. Stiles and Danny were tasting each other's precum on the other's tongue. They began to grind their erections on each other's hips as Daniel reached over to the stand to pull out a condom and lubricant. "Get on your hands and knees," Daniel ordered. Stiles sat up and turned himself over, presenting his ass in the air. Stiles felt as Daniel placed his hands on his ass, squeezing his cheeks, giving Stiles a gentle lap on the left one. But most importantly, Stiles felt the hot breath of Daniel's mouth on his hole, and the feel of a wet tongue lick around the muscular ring a few times before it dipped deeper into him, lapping him up from the inside.  Stiles whimpered in pleasure as Daniel lubed up Stiles from the inside with his mouth, giving him an extreme pleasurable sensation which only made Stiles want Daniel's cock inside him more. 

     After a few minutes, the mouth was removed and Daniel walked over to Stiles so he could watch Daniel put the condom on correctly, covering his entire girth. "Just so you know for certain it's on," Daniel said reassuringly.

     "Thank you," Stiles said. "Now lube it, and use it."

     "You say the nastiest, most demanding shit, Dylan," Daniel said as he popped open the lid and squeezed some lube onto his dick, giving it a generous coating before headed back to Stiles. The bed adjusted as Daniel climbed on it, and then a pressure started to press against Stiles's hole, expanding him. The pressure sunk deeper and Stiles grunted as Danny slid into Stiles completely.

     "Fuck," Stiles whimpered. 

     "You're so tight," Daniel said. "I can change that, don't you worry."

     Daniel wrapped his hands around Stiles's hips and removed himself nearly completely from Stiles before he headed back inwards. Daniel was taking it slow at first, giving Stiles the ability to adjust to the hot member in his ass. Stiles nearly purred at how good Daniel was making him feel. It felt great for Stiles. But it got even better when daniel brushed up against Stiles's prostate, making Stiles's jump a little. "That was the spot, Daniel. Fucking beat up the spot. Hit it faster," Stiles begged. Daniel sped up and was fucking Stiles faster, and harder. The sound of Daniel's pelvis smacking into Stiles's ass repeatedly was echoing up the room. Stiles was whimpering and moaning with every thrust Daniel gave. Stiles orgasmed quickly, without ever having to touch his cock. His semen oozed out of his penis as electricity energized his body. His legs trembled with the force that came with it. This was the first time Stiles had ever experienced an anal orgasm with another man. There was one other time only, and that was with a toy.

     "I just came already," Stiles huffed out.

     "Damn, Dylan. You must love this cock," Daniel said. "Show me how much you like it." Stiles began to push himself backwards on Daniel's dick, the both of them meeting in the middle in unison. "Yeah, work that ass, Dylan." Daniel slapped Stiles's ass again, making a small high-itched noise escape Stiles's lips. Daniel got down on Stiles's back, pushing them both completely to the bed. He wrapped his arms around Stiles like a hug and continued to thrust himself and push in on Stiles, who was now laying in a small pile of his now cold semen. Daniel was kissing Stiles's neck and nibbling on his ear all while fucking Stiles in a tight embrace. "You make me feel so good, Dylan. You're going to make me cum."

     "Just another minute please," Stiles whimpered. "Please just pound my ass a little more." Daniel nodded his head in the crook of Stiles's neck, their faces rubbing in together before Stiles adjusted so that they could kiss. A few more moments of humping Stiles and Daniel was moaning, trembling and twitching on Stiles. Stiles could feel all of Daniel shake on his body as he climaxed. Daniel stopped, caught his breath, and then slowly slid out of Stiles, becoming limp. He climbed out of bed and Stiles sat up, watching him redress and leave without a thank you. 

     Stiles felt a little weird after that. Even after a hookup, Stiles had been allowed to stay and cuddle or Stiles had allowed the other guy to stay the night. This was the very first time Stiles had a hookup and his partner left or abandoned him. And there wasn't even a thank you. Stiles knew why there was no thank you. One says thank you after a favor, after someone does something nice as a surprise. This wasn't a favor. This was a service. This is what Daniel paid for. He got what he wanted. That was the best sex of Stiles's life. Daniel had been so nice, so caring, only got rougher because Stiles wanted it. And that was the worst part. Stiles had been so open to Daniel. Daniel made him feel more like a person, less like an object. But not anymore. Now, Stiles knew what he was: a whore. He was just a fuck hole to use.

     He doesn't remember walking the few feet into the bathroom or starting the shower, he just knew that right now he was under the water, scrubbing himself vigorously, trying to make himself feel cleaner. He lathered up his ass the most, his hole still too sore and tender that it felt sensitive to the touch of Stiles's hand,and the rest of the water trying to cleanse it. Stiles let out a tear. He was in the shower for about an hour. He wandered back into the bedroom and looked at the bed he was just ruined in. He ripped the comforter off and kept it on the floor. Stiles was a little cold that night, trying to sleep. He figured a few nights would be like this.

* * *

 

      Stiles exited the fitness room and looked to see Ennis coming back with Kali's drink. Stiles quickly headed in the other direction to avoid encountering him after ruining his date. He squeezed past a few people before his phone began to ring. He reached into his pocket to pull out the phone.

FROM: JACKSON "COME UPSTAIRS TO MY ROOM. DANIEL IS HERE."

     Stiles took a deep breath and began to walk to that side of the house trying to text a reply.

IM ON MY- thud.

     Stiles had put his head up to look at the brunette woman he had just bumped into.  "I'm sorry, somebody texted me. I should have been more careful. Did you spill your drink? Is your dress ruined?"

     The woman chuckled. "No, no, it's ok. I'm a bit buzzed, I've been stumbling all night. It's no biggie. And besides, the drinks are unlimited here!" she exclaimed blissfully. "What's your name, kid?"

     Stiles hesitated. "Uhm, it's Dylan. And yours?" The woman gave him a strange smile. It was something less-than genuine.

     "It's Katherine. It's nice to meet you," she said as she extended her hand. "I hope you're having fun here. It's overboard in my opinion."

     "I agree one-hundred percent. I would stay and chat, but I'm actually trying to find my friend, so I'll have to run off," Stiles said.

     "No, go ahead," she said as she scooted out of the way for him. "Enjoy your evening!"

     "You too!" Stiles said as he gave a goodbye salute to her before heading down the hallway. Katherine smirked and pulled out her cellphone and began to type.

I MET THE STILINSKI KID. HE'S HANDSOME LIKE HIS FATHER.

     She took a sip of her martini and continued to walk down the hallway before her phone pinged. She held her phone up and read the text.

SO THEN? WHAT DO YOU THINK ABOUT THE SITUATION?

     She smirked and sat at the bar to request a refill before responding.

I THINK YOU'RE RIGHT ABOUT HIM.

     Katherine was given her drink and she took a sip of it before someone sat next to her.

     "Katherine! You made it!" Jackson exclaimed, hugging her. She smiled and hugged him back.

     "Of course I was going to come!" exclaimed Katherine. "After all, I'm a friend of the family, aren't I?"

**Author's Note:**

> Sorry this didn't have the picture of the house. Apparently screen shots don't work with full screen computer games? Also let me know what you thought bout the smut. I'm not the best, but I tried. There's more of that to come. And more drama! Tell me your thought on Katherine :O Tell me your thoughts on the feels :O Tell me EVERYTHING :O


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